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Volumn 63, Issue 18, 1998, Pages 6344-6347

Short Enantioselective Total Syntheses of the Piperidine Alkaloids (S)-Coniine and (2R,6R)-trans-Solenopsin A via Catalytic Asymmetric Imine Hydrosilylation

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EID: 0000550667     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980808q     Document Type: Article
Times cited : (80)

References (43)
  • 5
    • 85086526522 scopus 로고    scopus 로고
    • note
    • 2. See the Experimental Section and ref 1.
  • 29
    • 1542741180 scopus 로고    scopus 로고
    • note
    • Treatment of 5-bromovaleronitrile with n-propylmagnesium chloride provided a mixture that was 52% 5a by GC analysis (uncorrected for response factors). Reaction of n-undecylmagnesium bromide with the same bromonitrile gave a mixture that contained only 5% 5b by GC analysis.
  • 30
    • 1542741179 scopus 로고    scopus 로고
    • note
    • By employing benzene as a cosolvent during the Grignard reaction and performing the imine hydrolysis at 60°C instead of room temperature, we have been able to prepare the related 2-ethyl-3,4,5,6-tetrahydropyridine without isolation of the intermediate chloroketone in 67% overall yield after distillation: Yang, B. H.; Buchwald, S. L. Unpublished results. See also ref 10.
  • 39
    • 85086527660 scopus 로고    scopus 로고
    • note
    • 2: Hansen, M. C.; Buchwald, S. L. Unpublished results.
  • 40
    • 1542636001 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • Grashey, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6, p 245.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 245
    • Grashey, R.1
  • 42
    • 85086527704 scopus 로고    scopus 로고
    • note
    • 1H NMR) identical to previously prepared samples.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.